N-1-Naphthylcarbamic acid-2,4,5-trichlorophenol ester

ABSTRACT

N-1-Naphthylcarbamic Acid-2,4,5-Trichlorophenol ester is synthesized by reaction of 2,4,5-Trichlorophenol with 1Naphthylisocyanate. Product is useful for fungicide and herbicide, especially as a post emergence herbicide in agricultural formulation.

United States Patent Fooladi Dec. 30, 1975 [76] Inventor: Mike Mehdi Fooladi, Apt. 4-B,

Oakmont Manor Apts., Vicksburg, Miss. 39180 [22] Filed: Nov. 13, 1974 [21] Appl. No.: 523,496

[52] US. Cl. 260/471 C; 71/111 [51] Int. Cl. C07C 125/06 [58] Field of Search 260/471 C [56] References Cited UNITED STATES PATENTS 2,903,478 9/1959 Lambrech 260/471 C 2,945,877 7/1960 Zima et al 260/471 C Primary Examiner-James A. Patten [57] ABSTRACT is useful for fungicide and herbicide, especially as a post emergence herbicide in agricultural formulation.

1 Claim, No Drawings N-l-NAPHTHYLCARBAMIC ACID-2,4,5-TRICHLOROPHENOL ESTER DESCRIPTION OF THE INVENTION A new chemical compound, namely, N-l-Naphthyl- TABLE I Herbicidal Screening Invention Rate Mustard Pigweed Crabgrass Foxtail Corn Wheat Cotton Beans Compound Lbs./ A Pre Post Pre Post Pre Post Pre Post Pre Post Pre Post Pre Post Pre Post 2O G 0 5G 0 2G 0 2G 0 1G 0 l G 0 3G 0 3G l 0 0 4G 0 5G 0 1T 0 IT 0 1G 0 0 0 0 0 0 5 0 4G 0 5G 0 O 0 O O O O O O O 0 O 2 0 1G 0 2G 0 O O 0 0 0 O O O 0 O 0 The letter ratings in Table I are:

0 None Slight general necrosis Moderate general necrosis 36 Moderately severe general necrosis 40 Severe general necrosis 50 Death eneral necrosis IT Slight tip burn The described compound may be prepared by reacting one part of 2,4,6-Trichlorophenol with one part of I-Naphthylisocyanate in an inert solvent such as benzene, toluene, chloroform, or carbontetrachloride. The invented compound may also be prepared by reacting one part of 2,4,6-Trichlorophenol with two parts of phosgene followed by reaction of resulting intermediate with one part of l-Naphthylamine in an inert solvent.

The following example is illustrative of the preparation of the invention compound:

EXAMPLE I Preparation of N-l-Naphthylcarbamic Acid-2,4,5- Trichlorophenol ester: A mixture of 2,4,5-Trichlorophenol (20.0 g; 0.1 mole), l-Naphthylisocyanate (17.0 g; 0.1 mole) and I00 ml toluene was stirred and refluxed for twenty-four hours. The mixture was cooled then poured into 300 ml of cold water while stirring. the resulting solid material was filtered and dried to give 24 grams of N- l -Naphthylcarbamic acid-2,4,5-Trichlorophenol ester. M.P. l76C-178C.

Analysis for C, H NO Cl Analysis for C H NO Cl Theory C, 55.66% Found: C, 55.56% H. 2.73% H, 2.33% N. 3.82% N, 3.55% CI, 29.06% CI, 29.! 1%

FUNGICIDAL ACTIVITY OF N-l-NAPHTI-IYLCARBAMIC ACID-2,4,5-TRICI-ILOROPHENOL ESTER Soil Drench: Rhizoctonia sp. disease was mixed with a soil prepared from three parts loam and two parts sand.

The treatments were applied as a drench to a small flat with forty pea seeds.

A negative control with untreated soil and seeds and one with fungus treated SOIl and untreated seeds served as base line standards. All flats were watered uniformly and maintained in a controlled temperature and humidity environment. The percentages of germinating and growing plants were recorded and tabulated after three weeks in Table II.

TABLE II Fungicidal Screening Soil Drench Growing Pea Seeds Compound Rate Lbs/A Rhizoctonia Invented Compound 20 95 Compound I0 85 5Q Terraclor 20 95 Terraclor I0 90 Untreeatedinoculated 60 Untreated-sterile 95 soil I claim: 1. Compound having the formula 9 *a Cl o c N R 

1. COMPOUND HAVING THE FORMULA 